Ahh, fall. Who doesn’t love days filled with cozy sweaters, leaves that crunch underfoot, and the delicious smell of everything pumpkin spice? This season's warm and inviting vibes just make us feel like curling up in a big blanket and never leaving!

But with the changing weather, it’s time to slightly alter our wardrobe styles for the colder days ahead. As October rolls in, a great way to stay snug is to dress in stylish yet comfortable outfits appropriate for any activity in the fall.

The overall dress is a fall favorite fashion staple, and it goes so well with our favorite autumn activities. This particular style of dress is also often called a pinafore or jumper dress. Whatever you call it, these dresses are perfect for layering and building a cozy fall outfit.

Whether you’re planning an apple-picking outing, a romantic day date, catching up with friends over coffee, or window shopping, we have the perfect looks to keep you chic and cozy.

A Jumper Dress is an Easy to Pack Fall Outfit for Vacations

The photos of me in this blog post were taken during our fall October trip to New York City. A jumper dress is so easy to pack for autumn vacations because you can layer all kinds of tops and sweaters with it. On warmer days you can layer a t-shirt, and on colder days you can wear a sweater underneath. If it’s extra chilly, you can wear tights and tall boots to keep your legs and feet warm.

Pumpkin Patch Autumn Outfits

Dressing up for a visit to the pumpkin patch is a favorite fall pastime. And you know planning out your outfit is crucial because there will be lots of cute photos taken!

Consider a cozy overall dress over a thermal henley long sleeve top in a favorite fall shade like burgundy or rust orange. Add some touches of color to your outfit by accessorizing with a rustic patterned scarf or a hat.

Plus add a pair of practical but still very cute welly boots for meandering through the pumpkin patch. If there’s a chance of rain showers, bring along your colorful raincoat.

Overall Dress Style for Apple Picking

For outdoor activities like apple picking, an overall dress is a natural choice, because it’s slightly related to the traditional farmer’s overalls.

You can choose from a variety of fabrics and styles, such as denim, corduroy, plaid, and in mini-length or midi-length. Top it off with a plaid button-down flannel shirt or denim/chambray shirt for added texture and warmth.

Don’t forget to bring a large basket or bag to carry all those sweet apples home!

Halloween Jack-o'-Lantern Carving

Whether your a mom with young kids like me, or just a DIY crafting Halloween enthusiast, getting together to carve and paint pumpkins is a fall must-do.

Carving pumpkins can be messy business with all the squishy “pumpkin guts” and slippery seeds. If you’re carving outside in the breezy October weather, pair your pinafore dress with nylon tights and an outer layer cardigan. Add unexpected color with graphic and fall hued tights. Choose from autumn colors such as maroon, burnt orange, mustard yellow or forest green.

Romantic Day Date in a Pinafore Dress

Whether it’s a lunch date or an afternoon spent exploring the city, keep your pinafore dress look romantic and flirty. To complete the look, layer a chunky sweater underneath to keep you extra warm!

If you’re feeling extra sassy, put on a blouse with a colorful print or statement sleeves – something memorable and striking.

For an elevated evening look, switch to a dark-colored lace top and rock it with confidence! An over-the-knee boot can also be an excellent addition for extra style points, as well as jewelry pieces like short layering necklaces and earrings.

Fall Farmer’s Market and Harvest Festival Outfits

The fall season is known as harvest time for many popular crops and produce. There’s also many harvest festivals that take place around this time of year. Growing up in Half Moon Bay we had a huge Pumpkin Festival every year.

A basic or striped t-shirt under your overall dress is an effortless way to achieve the comfy vibes we all love in the fall. Layer on an oversized cardigan and accessorize with a cute beanie hat to keep you warm.

Crossbody bags are also a complimentary addition to your ensemble, as they’re practical and hands free (because you'll need your hands for eating the locally made pumpkin pie!).

Coffee date with friends in a Skirtall

Just because the weather is cooling down doesn’t mean you have to sacrifice fashion for warmth. Dress casually chic for your coffee catch-up with your besties by pairing a mini-length skirtall dress with a neutral or colorful turtleneck top.

For accessories, a wool beret can surely add a nice touch. Finish off your perfect outfit with a cute pair of ankle boots.

These comfortable and easy-to-style pieces will make you look stylish yet feel cozy enough to stay out all day. So go ahead and enjoy that extra-long chat over coffee!

Cute Thanksgiving and Friendsgiving Outfits

You’ve spent the whole morning cooking up a feast, and now it’s time to dress up and enjoy a good meal with friends and family. If you’re having a pot-luck style gathering, make a batch of my favorite cornbread recipe!

Jumper dresses are perfect for a big meal because they are not tight around the waist and allow plenty of room for your “food baby belly.” Style your jumper dress with a patterned top - think plaid, stripes, or floral prints for a fun yet sophisticated look.

Complete the outfit with your favorite pair of sneakers, flats, boots or loafers.

Take Instagrammable Pictures of Autumn Foliage wearing a Jumper Dress

Autumn is the perfect time to take pictures of the beautiful foliage and of course share them on your Instagram and TikTok. Show off your style with a jumper dress that adds charm and cozy vibes to your look.

Diversify your fall style by pairing the jumper dress with a Fair Isle sweater. This quintessential fall and holiday knit provides interest and texture with colorful patterns. Trust me when I tell you that this combo will make you picture ready!

Urban City Style Overall Dress

Hey hey cosmopolitan divas! For an edgier metro city fall vibe, wear a jumper, pinafore or overall dress made of genuine or faux leather. You can layer it over an oxford white button down shirt, a satin blouse, fitted lace or graphic tee. Finish the style with high socks and combat boots.